The Biggest Questions the Chicago Cubs Must Answer This Offseason

The Chicago Cubs will be faced with several decisions this offseason that have short- and long-term implications.

Some are more general in terms of spending or where to spend, but Chicago will also have to deal with impending free-agent or arbitration eligibles.

The Cubs are expected to be active after the conclusion of the World Series, and it will be interesting to see what issues they tackle first. Finding a manager will be the first priority, but what comes next?

General manager Jed Hoyer will likely approach Kevin Gregg and gauge his interest and his price tag. Given some of the calamity at the closer role and elsewhere this year with the Cubs, Gregg's price will certainly rise.

Let's take a look at the biggest questions facing the Cubs this offseason.

What to Do with Darwin Barney?

Harry How/Getty Images

Cubs second baseman Darwin Barney saw his average fall from .276 in 2011 to .208 in 2013. Despite being a Gold Glove second baseman, Barney has not lived up to expectations and regressed in each of the past two seasons.

The Cubs appear relatively content with Barney while some of the prospects in the minors develop, but is he worth holding on to over pursuing a veteran infielder? He may come at a reduced price on a one-year deal, but his position should be open to competition come spring training.

Should the Cubs Spend in the Free-Agent Market?

Jared Wickerham/Getty Images

The Cubs have the money to make a move this offseason, a big move. Last year, the team signed Edwin Jackson to a four-year deal worth $52 million. The Cubs have several vacancies that would benefit from an upgrade, but the team has shown restraint on the open market and appears content with internal options while prospects develop.

That may not be the case this year, as the Cubs will have to spend on Nate Schierholtz and Dioner Navarro anyway, so they may be more open to exploring the open market. Both Schierholtz and Navarro played well in 2012 and will seek pay raises.

Shin-Soo Choo is an interesting free agent but will be one of the highest-paid players this offseason, which may turn the Cubs away before the bidding gets underway. Time will tell.

An addition like David Murphy makes sense. He would be similar to David DeJesus and would probably accept a two-year, $10 million deal with the possibility of being traded to a contender if he performs well.

We'll see if the Cubs change course in their approach this offseason. Do you think they should?

Should the Cubs Re-Sign Dioner Navarro?

In 89 games this season, Dioner Navarro hit .300 with 13 home runs and 34 RBI. If Navarro is coming back, he is going to want to an everyday gig, at least one that guarantees 400 at-bats.

Whether there is one out there for Navarro or his price is right will determine league interest in the veteran backstop. The Cubs certainly like the way he played and would love to bring him back, but the price would have to be reasonable.

I know I'm not alone in supporting Wellington Castillo at catcher. The long-time Cubs farmhand may finally get a chance to be an everyday player in 2014, but the Cubs are mum on their long-term plans with him.

Who Will Be in the Rotation?

Tom Lynn/Getty Images

The top three positions in the Cubs rotation are set with Jeff Samardzija, Travis Wood and Edwin Jackson. Jake Arrieta pitched great when the Cubs acquired him with Pedro Strop for Scott Feldman, posting a 3.66 ERA in nine starts to finish the year.

The change of scenery proved effective, and he appears poised to hold a rotation spot in 2014. The final spot will come down to either a rookie, someone like Chris Rusin, or a free agent the Cubs sign.

Last offseason, there was speculation the Cubs would be players in the free-agent market, but the only blockbuster move they made was signing Edwin Jackson. They may look to add another free agent this year, leaving Jake Arrieta in a fight for the fifth rotation spot.

The Cubs do have several intriguing pitching prospects, some nearing the big league level. It is possible they will continue to search for options like Travis Wood or Jake Arrieta, inexpensive players with upside and some track record of success, while the minor league pitchers develop.

The pitching prospects in question are Kyle Hendricks, who was recently named Minor League Pitcher of the Year in the Cubs organization, and C.J. Edwards. Hendricks went 13-4 with a 2.00 ERA in 27 combined starts at the Double-A and Triple-A levels. He is expected to begin the year at Triple-A but could be an early call-up if he continues to dominate opposing hitters.

The other pitcher, C.J. Edwards, is only 22 years old and posted a combined 1.86 ERA in 24 starts in High-A between the Cubs and Texas Rangers organizations. He's expected to begin the year at Double-A and, depending on how he progresses, could face Triple-A hitters by the end of 2014.

The Cubs have plenty of reasons to be patient, but despite the hype and excitement around some of the Cubs prospects, all bets are off when it comes to minor league talent. The uncontrollable factors that could derail a player's progress or injuries are reasons why teams don't rest on their laurels waiting for prospects to mature.

A veteran arm who could potentially eat up innings would serve the Cubs rotation and bullpen well. Even if it is on a one- or two-year deal, the Cubs should exhaust those options before relying on internal options.

It's hard to see the Cubs going after a big-name free-agent arm given the vast majority of pitchers available this offseason are over 30 years old and Jeff Samardzija is two years from free agency and without an extension.

Find a serviceable stopgap and re-evaluate at the end of the season. That's been this teams M.O. the past two years anyway.

Should Mike Olt Start the Year at Triple-A?

A lot will depend on moves the Cubs make this offseason and what they envision as the makeup of the lineup going forward. If they find someone they like and want to give an opportunity, Mike Olt will likely begin the year at Triple-A and be evaluated much in the way Anthony Rizzo was in 2012.

If the only moves the Cubs make are bringing back Donnie Murphy and retaining Luis Valbuena, they will kick off a competition at second and third base involving Darwin Barney and Olt. Murphy and Valbuena can play both positions, so they could be serviceable from the bench as well. But if Olt can hit, he presents an exciting opportunity for the Cubs.

Either way, in 2014 Olt will be with the Cubs and given a real opportunity to take the third base job. Whether it happens in April or July will be sorted out as we get closer to spring training.

Should the Cubs Re-Sign Kevin Gregg?

Christian Petersen/Getty Images

Kevin Gregg really held the Cubs bullpen together this season. Signed within the first month of the season, Gregg came in and posted a 3.48 ERA in 62 games, his best year since 2010. He totaled 33 saves and quickly became relevant in closer discussions.

His service would be valued in the Cubs bullpen in 2014, but the Cubs appear ready to try Pedro Strop, who posted a 2.83 ERA in 37 games for the Cubs.

The Cubs hardly have any depth in the bullpen and will have to make some moves regardless of whether they keep Gregg.

Would it be more economical to rely on the depth that Strop provides with Gregg at closer or spend elsewhere and take a chance on Strop?

There are several names out there in terms of relief pitching, and the closer market is slightly deeper than in years past. Joaquin Benoit pitched great for the Detroit Tigers and would make a great closer for the Cubs. He's also versatile enough to set up or pitch anywhere, but after his successful year, he is likely looking for a closer job.

Do the Cubs Re-Sign Jeff Samardzija Now?

Denis Poroy/Getty Images

The Cubs may look to lock up Jeff Samardzija this offseason before his price can rise any higher. Samardzija is 17-26 over the past two seasons with a 4.07 ERA in 61 starts. He eclipsed 200 innings for the first time in his career in 2013 and struck out 214 batters, also a career high.

There is no question Samardzija has the stuff, but his consistency is certainly something of a concern as he hasn't fully put it together yet. He's hardly had a good offense or defense behind him.

He won't be a free agent until after the 2015 season, but unless the Cubs are looking to trade him, his price will only rise as we enter 2014, as media and fan interest increase.

In terms of leverage, the closer he gets to free agency the better it is for him. However, he's given every indication that he wants to discuss a deal, so will the Cubs bite and get something worked out?

It will most likely depend on how the free-agent market plays out and if the Cubs plan to be aggressive or not.

Who Is the Next Cubs Manager?

It appears San Diego Padres bench coach Rick Renteria has emerged as the favorite for the Cubs managerial gig, according to Matt Snyder of CBS Sports.

Just like team president Theo Epstein has pulled from Boston, GM Jed Hoyer is pulling from his former franchise, the Padres.

Renteria is a very experienced coach and baseball man, and has spent years in the Padres organization developing some of San Diego's young talent, a skill the Cubs are desperately seeking apparently, per Snyder:

He played in the minors in parts of 14 seasons and the majors in parts of five as a utility infielder. He then managed in the minors for several years before becoming a hitting coach in the Padres organization. He later returned to managing in the Padres system, being promoted to Triple-A and then eventually was promoted to a major-league coaching job in 2008.

There has been no confirmation of this report, so expect to see Dave Martinez, A.J. Hinch and Manny Acta's names still floating around. The Cubs would also like to interview Boston Red Sox bench coach Torey Lovullo, but he is currently tied up with the World Series at the moment.

Plus, the Cubs won't make an announcement during the World Series; that is usually frowned upon by league officials.

Lovullo would certainly help his chances if the Red Sox win the Series, but win or lose, Lovullo is as knowledgeable and respected as any baseball coach and certainly has a managerial job in his future.